Safrole

  1. Synthesis of 1-(3, 4-methylenedioxyphenyl)-1-butene-3-one from safrole. The synthesis of 1-(3, 4-methylenedioxyphenyl)-1-butene-3-one from Safrole has been done through conversion of allyl group to double bonds conjugated-ketone. Safrole was isolated from culilawan oil. The isomerization of safrole with KOH free solvent yielded isosafrole (72.82%), followed by oxidation of isosafrole with KMnO4 and the application of Tween 80 as catalyst yielded piperonal (72.30%). The Condensation reaction of piperonal with acetone by the molar ratio of piperonal and acetone 1: 6 and KOH as a catalyst and reaction time 2 hours followed by recrystalisation in methanol yielded yellow solid (84.21%).
  1. SYNTHESIS of 3.4-METHYLENEDIOXYPHENYL-2-PROPANONE from SAFROLE. The Synthesis of 3.4-methylenedioxyphenyl-2-propanone from safrole has been achieved through conversion of allyl group to secondary alcohol, followed by oxidation with pyridinium chlorochromate (PCC). The secondary alcohol has been achieved by two methods. The first method was formic acid adition reaction, followed by hydrolysis in aqueous ethanolic solution of potassium hydroxide. The second method was the oxymercuration-demercuration reaction of safrole. The addition reaction of safrole with formic acid yield safrylformate (34, 70%). The hydrolysis of safrylformate with 3M KOH produced safrylalchohol (73, 29%). The oxymercuration-demercuration reaction of safrole with Hg (OAc) 2-NaBH 4 gave (74, 37%) of safrylalcohol. The oxidation of safryalcohol with PCC gave 3.4-methylenedioxyphenyl-2-propanone as a main target in 71, 83%. The structure elucidations of these products were analyzed by FTIR, 1 H-NMR, 13 C-NMR and MS.
  1. SYNTHESIS OF SECONDARY ALCOHOL COMPOUNDS FROM SAFROLE AND METHYLEUGENOL. Synthesis of secondary alcohols compound from safrole and methyleugenol has been achieved through conVersion of allyl group to alcohol. The reaction of safrole and methyleugenol with mercuric acetate in aqueous tetrahydrofuran, followed by in situ reduction of the mercurial intermediate by alkaline sodium borohydride produced secondary alcohol namely safryl alcohol (71.25%) and methyleugenil alcohol (65.56%). The structure elucidation of these products were analyzed by FTIR, 1H-NMR, 13C-NMR and MS.
  1. Synthesis of safryl ketone from safrole. Synthesis of safryl ketone from safrole has been achieved through conversion of allyl group to secondary alcohol, followed by oxidation with PCC-Al2O3. The oxymecuration-demercuration reaction of safrole with HgSO4-NaBH4 yields safryl alcohol (66.38%) and the oxidation of safryl alcohol with PCC-Al2O3 yields safryl ketone (62.92%).